SA522431717B1 - Siloxane Derivatives of Amino Acids Having Surface-Active Properties - Google Patents

Abstract

The present disclosure provides siloxane derivatives of amino acids that have surface-active properties. The amino acid can be naturally-occurring or synthetic, or they may be obtained via a ring-opening reaction of a lactam, such as caprolactam. The amino acid may be functionalized with a siloxane group to form a compound that is surface-active and has surfactant characteristics. The compounds have low critical micelle concentrations (CMC) as well as the ability to lower the surface tension of a liquid. Fig 2.

Description

Siloxane Derivatives of Amino Acids Having Surface-Active Properties Full Description

Invention background

The current disclosure relates to siloxane derivatives from amino acids and methods for their synthesis, where siloxane derivatives have surface-active properties.

Surfactants are molecules with surface-active properties and are an important class of molecules with highly foaming properties. Surfactants may be uncharged, binary or cationic. or anionic ©80100. These Ble compounds are often diamophilic molecules with a hydrophobic, insoluble 'ad' group and a hydrophobic, soluble 'ad' group

0 in the water. These compounds may adsorb at the interface; Such as the interface between lil (liquid Oley or liquid and solid. In Alla there is an interface between water and oil; the hydrophobic head group extends in celal) while the hydrophobic tail extends into oil. When added to water, the head assembly extends its hydrophobicity into the water; While the hydrophobic tail extends in the air. The presence of a surfactant disrupts the intermolecular interaction between water molecules; And replace it with weaker interactions between water molecules and matter

5 surfactant This results in a lowered surface tension 007 and can also stabilize the interface. At high concentrations including USN, surfactants can form agglomerates to limit exposure of the hydrophobic tail to the polar solvent. One such molecular grouping is Abell, where the molecules are arranged in Ball with hydrophobic tails

Hydrophobic tails 0 inside the ball and hydrophilic heads on the outside to interact with a polar solvent.

The effect of a particular compound on the surface tension and concentration at which it forms micelles may be specific properties of a surfactant Surfactants are widely used in commercial applications in formulations ranging from detergents to hair care products to cosmetics . Compounds with surface active properties are used as soaps, detergents, and lubricants; wetting agents; foaming agents; and diffusion agents, among other things. Thus, there is continuous dala for identifying and synthesizing these compounds. However; From its structure alone it can be difficult to predict whether a particular compound will have surface—active properties, let alone other important properties such as Kalin 0 adsorption; minimum achievable surface tension; and/or the ability to wetting non-hydrophobic and/or non-oily surfaces; which is also an integral part of whether the compound will turn out to be a useful surfactant. Some amino acids and their derivatives (for example, JE) are foamed as building blocks for surfactants, but the choice of amino acids to be used is far from intuitive. Likewise, from 5 it is known that some 51078065 siloxanes have surface-active properties" But again, predicting which siloxane will be effective is very challenging. The synthesis of these compounds adds another layer of difficulty due to differences in solubility that are attributable to different elements and moieties present in the same molecules. There is still a need for Highly effective surfactants that can easily be manufactured on a commercial scale by direct methods.0 US Order #2008152540 discloses new and improved packaging systems for storage of Jia cationic ophthalmic devices, cationic contact lenses, and these packaging methods Cationic ophthalmic devices with solutions for improving daly lenses during wear.In particular, the present invention is directed to a packaging system for storing a cationic ophthalmic device in a solution comprising an effective amount of anionic polymer 25 8010016. These solutions should be applied to the surface of lenses that are not in use for long periods

of time; which leads to a modification of the surface that persists in the eye; Which can provide a huge improvement in the wetting properties of new lenses used for the first time; Furthermore it; several hours after inserting the lens; This prevents drying and improves lubrication. US Application No. 2007142583 relates to polymeric compositions useful in the manufacture of biocompatible medical devices. More specifically, the present invention relates to certain cationic monomers capable of polymerization to form polymeric compositions having foamy physical properties useful in the manufacture of ophthalmic devices. These properties include the ability to extract hydro-polymerized medical devices. This avoids the use of organic solvents as is usual in the art. Polymeric compositions 0 include cationic hydrophilic siloxanyl monomers . ER 0436359 discloses compound A of formula (([(RsSiO), SiR (CH,)a]bN'R's —bX" where R is an alkyl radical with 1 to 6 kreon atoms 68+000; R' is an alkyl or aryl radical A/81 containing a 5-carbon atom carbon atom one to eighteen atoms; X is chloride bromide iodide 00006 nitrate or 507 is a died integer from one to ten; and an integer with a value of two or three Lia discloses a method for reducing the surface tension of a Sle solution 8006005 whereby an effective amount of one of the compounds described above is added to the aqueous solution 0 GENERAL DESCRIPTION OF THE INVENTION The present disclosure provides siloxane derivatives of Amino acids that have surface active properties ©5011308-8017._ The amino acids may be natural amino acids or synthetic amino acids, or they can be obtained through ring-opening reactions of molecules Jie lactams eg caprolactam

caprolactam Amino acids can be used with different types of clean siloxane to form lS) with surface-active properties in a distinctive way These compounds may contain low concentrations of the critical micelle (CMC) Critical micelle concentrations and/or the ability to lower the surface tension of a liquid Surface tension of a liquid 5 The current disclosure provides compounds of the formula | Below: y lu amat ene a 1 1 l l l 3 0 {Ha 1SI0. J Np 1 rt IN = declare almagorgo OR form a where RY and R? can be the same or different “and contain at least one group selected from the group All consisting of an alkyl” C1-C6 alkyl Optionally the alkyl 0 01-06 may include one or more oxygen, nitrogen, or sulfur 501007 atoms or groups that include at least one of these atoms; The alkyl chain may optionally be substituted with one or more substitution groups selected from the group consisting of hydroxyl amino camino camido sulfonyl sulfonate creonyl Al68+001 creoxyl carboxyl and scarboxylate 5 « integer from 1 to 12; Optionally the final nitrogen RY is also substituted, where RY La) is from the group consisting of hydrogen, oxygen and hydroxyl alkyl Jif 01-06 ; An optional counterion may bind to the compound, and if it exists; The anti-ion can be chosen from the 0 group consisting of chloride, bromide, and iodide 100106. All additional compounds provided by the current disclosure are compounds with the formula tla

DSH ED A 1 Co L (HChSI0.yd TN 7 SPAD) (FSCS Re 0 formula la where RY and #8 can be the same or different; They include at least one group selected from group ll consisting of an alkyl “C1-C6 optionally alkyl 01-6 can include one or more oxygen or nitrogen atoms or groups 5 or a sulfur containing at least one of these atoms; the alkyl chain may optionally be replaced by one or more substituent groups chosen from the group consisting of the camino amino camido hydroxyl sulfonyl creonyl sulfonate Al68+001 carboxyl and scarboxylate mM represents an integer from 1 to 6; the final nitrogen is optionally additionally substituted by R10 where RO laa) of the group consisting of hydrogen, oxygen 0 and the C1-C6 alkyl hydrates where the alkyl chain is optionally replaced by one or more substitution groups chosen from the group consisting of ccarboxyl caroxylates ccarboxylate and sulfonate, and an optional counterion ion may be attached to the compound, and if there is one, the counterion 5 can be chosen from the group All consisting of chloride, bromide, and iodide, the additional compounds provided by it The current disclosure consists of compounds with the formula A: Glutatta yama i 3 1 b" ( i and znawk a N on A - ke from Ea ak TIN to FE N 1 um HES 0 Ib formula

where RY and R? can be the same or different” and contain at least one group

Selected from the group All consisting of an alkyl «C1-C6 alkyl optionally may include an alkyl

01-6 contains one or more oxygen or nitrogen atoms or groups

or Sulfur 501007 containing at least one of these atoms; The alkyl chain can be substituted

alkyl 5 optionally with one or more substituent groups chosen from the group consisting of

Hydroxyl chydroxyl amino camino amido camido sulfonyl sulfonate “sulfonate”

Creonyl Ala 68+001 » carboxyl and scarboxylate

m is 5;

The final nitrogen is optionally substituted further with 3g 0 where 0 is chosen from the group consisting of hydrogen, oxygen 007/9617 and an alkyl -61

(C6 where the alkyl chain is optionally substituted by one or JST of the substituent groups

Selected from group All consisting of carboxyl creoxylate «carboxylate

¢sulfonate and

An optional counterion ion may bind to the compound, and if found, the counterion 5 can be chosen from group All consisting of chloride, bromide, and iodide

iodide

The other compounds provided by the present disclosure are still those of the formula Where

Lg and R? are methyl

All other compounds provided by the current list are compounds with the formula ; 17 Cua is 5.0 Still other compounds All provided by list Jal are compounds of the formula

a where me and “” are methyl

However, the other compounds given by the present disclosure are compounds of the formula

hydrogen is hydrogen RY where lb

Other compounds provided by Jal are compounds of formula Ib

The antiion, cOUNterion, is from the group consisting of chloride and bromide.

and iodide 100106.

Additional compounds provided by the Mall list are compounds with formula A where the ion is

The countererion is chloride

Other compounds provided by the list all are compounds of formula 0 ¢ where R is ?

It is methyl 0160.

The other compounds provided by the present disclosure are compounds of formula 0a; where the ion is

The countererion is iodide 100106. 0 Still other compounds provided by the Jal detection are compounds of the formula

A where RY is oxygen

Additional compounds provided by the present disclosure are compounds of formula 0a; where

3 is an alkyl 66©-01; Substituted for sulfonate

One identified compound provided by the present disclosure is 6-(1-amino-dimer)—N- ) -3- 5-(1,1.1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy) Trisiloxane-3-yl)propyl)

Hexaneamide 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-)

(((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)hexanamide ; It has the following formula:

OSi(CH (HsC)sSI0.L (CHa): \ (H3C)3Si0" 7 ~~ hha NT o

The second specific compound presented by the present disclosure is 6-(dimethylamino) =N- ( -3- 0 (1,1.1, 5,5,5-hexamethyl-3-((trimethylsilyl)oxy)tri) siloxane-3-yl)propyl)

Hexaminium chloride 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-)

(((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)hexaminium chloride ¢ has the following formula: © : (HiC),SI0. 3 C18 0 © Cl (H3C)3Si0” ~~ N\ hhh N 7 H 0 The third specific compound presented by the present disclosure is 36-((3-(1,1.1,5,5,5-hexamethyl-) 3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amine)-NNN-lp-methyl-6-oxohexane-1-aminoiodide 6-((3~(1,1,1) ,5.5.5-hexamethyl-3- 3 (((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan—1-aminium iodide; It has the following formula: © : 1 ® § Wi (HiC)S10.hdd NC p dd (HaC)sSiO™ | 6 0 The fourth specific compound presented through the present disclosure is 6-((3- (1,1.1, 5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)proyl)amino) - NIN = trimethyl-6-oxohexane-1-amine oxide 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan— 3-yl)propyl)amino)-N,N-dimethyl-6- oxohexan—1-amine oxide « has the following formula: 0 and (HACHSI0 NC HACHSI0 NC HACHSI0 NAURI 5© | . The specific compound The v provided by the present disclosure is 4-((6-((3-(1,1.1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino) - 6-oxohexyl)_dimethylammonio)butane-1-sulfonate-1,1,1,5,5,5)-3)-6)-4

— 0 1 — hexamethyl-3—(((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)-6- ‎oxohexyl)dimethylammonio)butane-1-sulfonate « has the following formula: OSi(CH) M 0 1 L 2° (Hi0)810. ‎(H3C)3Si0” ~ TON dhe 3 0 The sixth specific compound presented through the present disclosure is 5 -((6-((3- (1.1.1, 5,5,5- hamsa-methyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)pentane 0 1 sulfonate-5,5,5.1 , 1 , 1)-3))-6))-5 hexamethyl-3—((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)-6- oxohexyl)dimethylammonio)pentane-1-sulfonate It has the following formula: OSi(CH (HiC)SI0.L +8 1 ® © NT ANN (H3C)sSI0™" ~~ YO N SO, \ 7 0 0 using the above features Other detection features and the method for achieving them are clearer and will be better understood by reference to the following description of the samples taken in conjunction with the accompanying graphics. chloride at pH = 7, as shown in Figure 2. A graph of the surface tension versus the concentration of the surfactant. Figure 3 shows a graph of the dynamic surface tension as a change in surface tension versus time of the surfactant 3 as shown. Described in Example 2b.

— 1 1 — Figure 4 plots the surface tension versus concentration of the surfactant Figure 5 plots the dynamic surface tension as change in surface tension versus time of surfactant 4 as described in Example 3b.

Figure 6 plots the surface tension versus concentration of the surfactant Figure 7 plots the dynamic surface tension as change in surface tension versus time of the surfactant 5 as shown in Example 4b. Detailed description:

0 as used here the phrase 'within any specified range between any two of the preceding values' literally means that any range can be selected from any two values listed before this statement regardless of whether the values are in the lower level part of the list or at the top of the ASE For example, a pair of values can be specified from two lower values; two higher values; or a lower value and a higher value. As used here the word 'alkyl' means any saturated carbon chain; lly may be a string

5 straight or branched. As used here, the phrase 'surface-active' means that the conjugate is capable of lowering the surface tension of the medium in which it is dissolved; and/or surface tension with other phases; And therefore; May be absorbed upon liquid/vapor and/or other interface surfaces. The term "surfactant" can be applied to Jie of this compound.

In terms of inaccuracy, the terms 'about' and 'nearly' may be used interchangeably to refer to a measurement that includes said measurement and which includes Load any measurements that are reasonably close to the specified measurement. Measurements that are reasonably close to said measurement deviate from The said measurement is of a reasonably small amount as easily understood and ascertained by skilled personnel

Ordinary in related fields. These deviations may be due to measurement error or minor adjustments made to improve performance; For example. in the event it is determined that individuals having ordinary skill in the relevant areas would not be able easily to ascertain the values for such reasonably small differences; The terms “about” and “Wl” can be understood to mean plus or minus 9610 from the stated value. The current disclosure provides siloxane derivatives of amino acids. Amino acids may be natural or synthetic amino acids; Or it can be obtained through ring-opening reactions of Jie-lactams molecules, for example, caprolactam. surfactants and wetting agents; For example. In particular; The present disclosure provides compounds of the formula | shown below: Ben and (Hysol Rr l Shoo yr Nakak and Zanawa) RY 0 formula where R25 RY can be the same or (piling) and include at least one group selected from the group that makes up of an alkyl “C1-C6 alkyl Optionally the alkyl 5 01-06 may include one or more oxygen, nitrogen, or sulfur atoms or groups 501503 that includes at least one of these atoms; the alkyl chain may optionally be replaced by one or more substituent groups selected from the group consisting of hydroxyl amino camido camido sulfonyl sulfonate creonyl A68+001 carboxyl creoxyl and scarboxylate 20 « integer from 1 to 12;

— 3 1 — Optionally, the final nitrogen, RY, is also substituted, choosing from the group consisting of hydrogen, oxygen, and hydroxyl talkkyl C1-C6 (<li, and Associated with the compound is an optional counter ion counterion, and if aang, the counter ion 5 can be chosen from the group All consisting of chloride, bromide and iodide. The current disclosure also provides compounds with the formula tla Sk CHa if live a 0 Qom SITY l 348 ( 050 RE la la exponential hi s rem HCHER0T + 0 formula la where can be l and R? the same or different” Pliny has at least one group 0 selected from the group consisting of an alkyl “C1-C6 alkyl Optionally the alkyl 01-6 can include one or more oxygen atoms or groups oxygen, nitrogen or sulfur 501007 that includes at least one of these atoms; the alkyl chain may optionally be replaced by one or more substitution groups selected from the group consisting of the hydroxyl amino camino amido camido sulfonyl sulfonate 5-carbonyl sulfonate ccarbonyl carboxyl and scarboxylate croxylate representing 177 integers from 1 to 6; The final nitrogen is optionally additionally substituted with RY ; where is ROL) from group consisting of hydrogen, oxygen, and an alkyl C1-C6 where the alkyl chain is optionally substituted by one or more selected substituent groups 0 of group All consisting of carboxyl creoxylate carboxylate sulfonate ¢sulfonate and

— 4 1 — An optional anti-ion, counterion, may be associated with the compound, and if aang, the anti-ion 07 can be selected from the group consisting of chloride, bromide, and iodide. In addition, the present disclosure provides compounds with the formula ib WHOM Mara (HC)SO Calg Pa SE ee, JN SHR AA UN Corrected Gothic 0 Formula A

where L and R? can be the same or different” Pliny has at least one group selected from group ll consisting of an alkyl “C1-C6 alkyl Optionally can include an alkyl 01-6 on one or more oxygen, nitrogen, or sulfur atoms or groups 501007 that includes at least one of these atoms; The alkyl chain 0 can optionally be substituted with one or more substituent groups selected from the group consisting of hydroxyl amino camido camido sulfonyl sulfonate

Creonyl Ala 68+001 » carboxyl and scarboxylate

m is 5;

The final nitrogen is optionally substituted further with 3c0” where 5 is chosen from the group consisting of hydrogen, oxygen 007/9617 and an alkyl -61

(C6 where the alkyl chain is optionally replaced by one or more substituent groups

Selected from group All consisting of carboxyl creoxylate «carboxylate

¢sulfonate and

An arbitrary counterion ion may bind to the compound, and if found, the counterion 20 can be chosen from the group consisting of chloride, bromide, and iodide

iodide

— 5 1 — One identified compound provided by the present disclosure is 6-(dimethylamino) -N-(-3-(1,1.1,5,5,5-hexamethyl-3-((trimethylsilyl)) oxy)trisiloxane-3-yl)propyl)hexaneamide 6—(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy) trisiloxan—3-yl)propyl)hexanamide (surfactant 1); It has the following formula: ro and coqsii (H3C)3Si0” ~~ hdd NT 0 A second specific compound has been introduced by the present disclosure which is 6-(dimethylamino) N= ( -3- (1.1.1 , 5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)proyl)hexaminium chloride 6-(dimethylamino)-N-(3-(1,1,1,5, 5,5-hexamethyl-3- (((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)hexaminium chloride 0 (surfactant 2(«) has the following formula: © : (HiC)SIOg ro y @ Cl ONT > (HC)S10™> 11 0 A third specific compound has been introduced by the present disclosure which is 36-((3-(1.1.1, 5.5.5-hexamegal-3-() Trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino) - NINN-5-trimethyl-6-oxohexane-1-aminoiodide 6-((3-(1,1,5,5, 5-hexamethyl-3— 3 (((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)-N,N,N-trimethyl-6- oxohexan—1-aminium iodide (3-surfactant) ); has the following formula: © : © 0 l a (H3C)sSi0"> ~~ he NC 57

A fourth specific compound was introduced by the present disclosure which is 6-((3-(1,1.1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino) = NIN - Trimethyl-6-oxohexane-1- .| oxide | Amine 6-((3-(1,1,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)-N,N-dimethyl-6- ‎oxohexan—1-amine oxide 5 (surfactant 4); It has the following formula: (H:0);50, 7°" 1 _ (HyC)aSi0” TYTN © | 0 in the above structure; the notation NO” is intended to convey the non-ionic bonding reaction between nitrogen And oxygen, a fifth specific compound was introduced through the current disclosure, which is 4-((6-((3- )1.1.1 5.5.5- 0 hexamethyl-3-((trimethylsilyl)oxy)trisiloxane -3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate-1,1,1,5,5,5)-3)-6)-4 hexamethyl-3 —(((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)-6- dls) oxohexyl)dimethylammonio)butane—-1-sulfonate for surfactant 5) has the following formula: nose _ a (H3C)3Si0” TON 0 A sixth specific compound was presented in the present disclosure, which is 5-((6-((3-(1,1.1, 5,5,5-hexamethyl-3-((trimethylsilyl)) oxy)trisiloxane-3-yl)propyl)amino)-6-oxo(dasa dimethylammonio)pentane-1sulfonate-1,1,1,5,5,5)-3)-6)-5 hexamethyl-3—((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)-6- oxohexyl)dimethylammonio)pentane—1-sulfonate 0 ; It has the following formula:

— 7 1 — OSi(CH 9 ® a 0% 3 (HAC)SIO. ach ah N SO, ah h Ah ~~ a waqurui) lah 0 These compounds can be synthesized in different ways. One such method involves Jolin an amino acid such as an L-1-alkylated amino acid or =N constituent”; With siloxane to convert the -© ends of an amino acid into the desired siloxane derivative. The N-terminus of the amino acid may also be methylated; alkylate or oxidized to produce a quaternary amine or oxide—“N,” for example. The amino acid may be naturally or synthetically produced or may be derived from a dactam ring-opening reaction such as caprolactam The ring-opening reaction may be either a bins reaction with an acid or an alkali; An example of an acid catalyzed reaction is shown below in Scheme 1. 0 Scheme 1 0 T2590 Je NH except H,0 HO 2 The amino acid may contain less than 1 or as many as 12 atoms between the two ends- CN -. The alkyl chain may be branched or straight. The alkyl chain may be interrupted by nitrogen, oxygen, or sulfur 707a5. The alkyl chain may also be substituted with substituent 5 and one or more substitution groups selected from the group consisting of hydroxyl hydroxyl amino camino camido sulfonyl sulfonate carboxyl sulfonate carboxylate croxylate nitrogen may be N-dilgllnitrogen is chained or alkylated with one or more J Cle gana groups of an al kyl . For example ¢ the amino acid could be gle amino acid from 6- (Good din) 6-(dimethylamino)hexanoic acid 0.

— 8 1 — Siloxane can be replaced by one or more alkoxy groups such as methoxy, ethoxy, JSOPrOPOXY, tertiary butoxy, and others. Wad can replace the siloxane with one or ST of the alkyl groups ; propyl Jug ll Jie where the alkyl group 5 may also be substituted with a suitable functional group to allow the coupling of the siloxane to an amino acid such as nitrogen 01009©1. For example; The siloxane may be a 3- sid Jug tris(trimethylsiloxy)silane .aminopropyltris(trimethylsiloxy)silane—3 The siloxane derivative of the amino acid can be synthesized as shown below in the diagram 2. As described; 6-aminohexanoic acid 8010-6 aminohexanoic acid 0 is treated with formaldehyde in formic acid upon reduction to obtain 6-(dimethylamino) acid G5. (dimethylamino)hexanoic 8610-6 “li glass all carboxylic acid is conjugated to 3- aminopropyl(trimethylsilane)silane by reversion of toluene to give a siloxane derivative required. Scheme 2 9 2 OH ric sa9 for atac HOSA yy, ma 3 return 0 g05 a b 1 ag OBICH a a a mm OH s ECOG series - io gy Fao 1 a Rv 8 ' F 38 4 L »Ala Laaaa Chg 0 M " Il Aulwin Nitrogen can be derived at the end - not also to modify or improve the water solubility and surface - active properties. A synthetic scheme for the sample is shown below in Scheme 3 where it is processed

— 9 1 — nitrogen, at the -N end, with hydrochloric acid to give the corresponding hydrochloride salt. R Hel (HsC)SI0~d;RN @ R (HsC)sSiO YT J OTN, R 0 0 0 06050 2g 0 Nitrogen with the N-terminus can be treated with an alkylating substance. cola where the N-terminal nitrogen is treated with methyl iodide to give the corresponding quaternary amine salt. oN ® Ri for Ng A (HsC)sSi0~g; (HyC),Si0 ry CHal | tons > NG, CHa 0 _nitrogen can be treated with the N-terminus using hydrogen peroxide hydrogen 56 in water upon return to yield the corresponding N-oxide, as shown in the synthetic sample diagram below; Scheme 5. {HG Ng Aa Solution H 0 TN 1 Ayy I: 8 Absorbents” and TAL {H;2,8iC i 15 Jal detection compounds show surface-active properties. These can be measured Characteristics and describe them in different ways. One way in which Al surfactants can be described is as critical micelle concentrations (CMC).

CMC is a surfactant concentrate at which micelles form; And above it all are integrated

Additional surfactants in micelles.

With increasing sald concentration of the surfactant the surface tension decreases. Once the

The entire surface is overlaid with surfactant particles; Micelles begin to form. represent these

5 point Low critical micelle concentrations (CMC) CRITICAL MICELLE

CONCENTRATIONS plus minimal surface tension. Adding more will not affect

It is a surfactant on a surfactant. So CMC can be measured by observing

Change in surface tension as a function of surfactant concentration. One way to measure this

The value is the Wilhelmi Panel method. The Wilhelmi plate is usually a thin plate of iridium 0 and platinum attached to a balance by a wire placed perpendicular to the surface

interface between air and liquid. The balance is used to measure the force exerted on the plate by wetting.

This value is then used to calculate the surface tension (/) Ga, for equation 1:

y=F/l cos 0 : 1 equation

where | equals the wetted circumference (20 + 2W where /la and d are the thickness and width of the plate, respectively) and 0 08©; The contact angle between the liquid and the plate is assumed to be 0 in the absence of literature value

existing.

The variable AT used to evaluate the performance of a surfactant is the dynamic surface tension. Stress

Dynamic surfactant is the surface tension value of a given surface or interface lifetime. In the case of liquids

additive surfactants; This can differ from the equilibrium value. 0 grater after surface production; The surface tension is equal to that of a pure liquid. as described above;

Surfactants reduce surface tension; So; Tension decreases

surface until the equilibrium value is reached. The time required to reach equilibrium depends on the rate

Diffusion and adsorption rate of a surfactant

— 1 2 — One of the methods by which dynamic surface tension is measured is based on a bubble pressure surface tensiometer. This device measures the maximum internal pressure of a gas bubble that forms in a liquid on a Gob capillary tube. The measured value corresponds to the surface tension at a given surface age; It is the time from the onset of bubble formation to the occurrence of maximum pressure. Surface tension dependence on surface age can also be measured. Surface active compounds can also be evaluated by their ability to hydrate on solid substrates as measured by telarm angle. Laie The liquid droplet comes in contact with a solid surface in the medium of Jia (ll air ¢ a tri-phase line forms between the liquid, gas and solid. The angle between the jab is described as a unit of surface tension, which acts at the triphase line and the tangent at the liquid droplet; And the surface has an angle of contact 0. Contact angle (also known as wetting angle) is a measure of the wettability of a solid by a liquid. In the case of full hydration, the liquid is completely spread over the solid and contact gh is 0 degrees. Wetting properties are measured Bale For a given compound at a concentration of 1 -0 1# low critical micelle concentrations (CMC) CRITICAL MICELLE CONCENTRATIONS However, it is not a concentration-dependent property and therefore measurements of wetting properties can be measured at higher or lower concentrations. Contact to measure contact angle For a sessile droplet of liquid on a surface Possible applications for the surface-active compounds in the present disclosure include formulations for use 0 as shampoos; hair conditioners and detergents; non-(aid) rinse solutions and floor and carpet cleaners; and cleaning agents for graffiti removal walls” and wetting agents to protect crops; Crop protection aids and wetting agents for spray paints.

— 2 2 — It will be understood by a person skilled in the art that small differences between compounds may result in different alsa of the Surfactant so vastly that different compounds can be used with different substrates; in different applications. The following unlimited models are provided to illustrate the different properties of different surfactants. In Table 1 below, the short names of surfactants are associated with their corresponding chemical structures. Table 1 Surfactant Formula and Name Surfactant (HiC)SIOL oo" H True Love > (HoClaSi0™ | 6 6- (Dimethylamino) (La -1,1,5,5,5) -3- ( -N- reductase (Ztm. 1©- (dimethylamino) JIT) TNT a miphyl-3-((trimethylsilyl)oxy)trisiloxane-3-1-hexane Amide 6—(dimethylamino)-N—(3— surfactant 1 yl)propyl)hexane amide 37 ( ) no ( (1,1,1,5,5,5-hexamethyl-3-) (trimethylsilyl)oxy)trisiloxan—3— yl)propyl)hexanamide © OH: 0 ® Cl 2 stimuli and its aroma - the correct advice is a response > and Tquruwi) a hypotonic substance o | TH surfactant. 6-(Dimethylamino) -N- ( -3-(1,1.1, 5,5,5-hexa surfactant 2 ) ) . Miphyl-3-((trimethylsilyl)oxy)trisiloxane-3- yl)propyl)amino)AE-1L N=methyl-6-oxohexane-1-

— 3 2 — Aminochloride 6-((3-(1,1,1,5,5,5-hexamethyl-3) ((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)- N,N-dimethyl-6-oxohexan—1-aminium chloride © . (HiC)sSIO.

J rok 0 ® | Tr SN] and roy 1 6 surfactant 6-((3-(1,1.1, 5,5,5-hexamethyl-3-((trimethylLol)silyl)oxy) trisiloxane-3-yl)propyl)amino) = N,N,N 3 surfactant -trimethyl-6-oxohexane-1-aminoiodide-6((3-(1,1,1,5,5) ,5-hexamethyl-3- (((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)- ‎N,N,N-trimethyl-6-oxohexan—-1-aminium iodide J ok 1 Dwarf Al-Sahs Al-Hass (HaC)sSIO™ <0 | 0-((2-(1,1.1, 5.5.5-hexamethyl-3-)(tray) surfactant 6-((3-(1,1.1, 35.5.5-methyl-3-)) tri-Hise I silyl) oxy) trisiloxane-3- yl) propyl) amino) - NN ) - trimethyl-6-oxohexane-1-amine oxide -3))- gl 4 surfactant methyl 6-oxohexane 1 amine O7((37 (1,1,1,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)- N, N-dimethyl-6-oxohexan-1-amine oxide OSi(CH3); .. (H3C)sSiO.

J.

H ® © Ls surfactant and 50 N dh N dh rb a distributed ( (H 0 ) surfactant 5 4 - ((3- (1,1.1, 5,5,5--3-hexamethyl) - ((Trimethylsilyl)oxy)trisiloxane-3-yl)proyl)amino) -

— 4 2 — 6-oxohexyl)dimethylammonio)butane-1-(4-((6-(((3-(1,1,1,5,5,5-hexamethyl-3))(((trimethylsilyl)) sulfonate) (oxy)trisiloxan—3-yl)propyl)amino)- 6-oxohexyl)dimethylammonio)butane-1-sulfonate Each of the five compounds are effective as surface-active agents and useful as wetting or villi-forming agents; dispersants; emulsifiers; detergents; among other applications. Surfactants 1 and 2 are candidates for use in a variety of formulations of personal care and surface cleaning products as foaming or wetting agents. The surfactant 3 is cationic. These surfactants are useful in both the applications described above and some other special applications Jie surface treatments; such as personal hair care products; They can also be used to generate water-repellent surfaces. surfactant 4 is nonionic; (Sarg) Use in shampoo Surfactant 5 is a substance with dual charges. These surfactants are useful as co-surfactants in all the applications described above. The amount of compounds disclosed here may be and used in reduced formulations such as les 5 0.001 wt % »about 960.05 wt » about 960.1 wt » sa 960.5 wt »about 1 wt » ; about 2 96 wt ; or about 5 96 wt ; or up to about 8 96 by weight about 10% by weight »about 15 96 by weight » about 20 96 by weight , or about 25 96 by weight , or within any specified range between either of the above values Examples

— 5 2 — Nuclear magnetic resonance spectroscopy JAe (NMR) was performed on a 500MHz Bruker spectrometer. Critical micelle concentrations (CMC) were determined by the Wilhelmi plate method at 23 °C using a surface tensiometer (DCAT 11) DataPhysics Instruments (GmbH DataPhysics equipped with a PEI plate) The dynamic surface tension was determined with a scale The surface tension of the Kriss “Kriss BP100” bubble pressure bubble (GmbH) at 23 deg. Contact angle was determined using an optical contact angle goniometer (DataPhysics GmbH (OCA 15 Pro) equipped with a digital camera. Example 1a: Synthesis 6- SE)methylamino) N= ( -3-(1,1.1, 5,5,5-hexamethyl-3-((trimethyl0myl)oxy)trisiloxane-3-yl)propyl)hexane amide 6—(dimethylamino)-N—(3- (1,1,1,5,5,5-hexamethyl-3~((trimethylsilyl)oxy)trisiloxan—3- yl)propyl)hexanamide (1-(dimethylamino) surfactant) =N- ( -3- (1,1.1, 5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3- yell) broyle) amino) - no; -N dimethyl-6-oxohexane-1-amino salt -1,1,1,5,5,5)-3))-6 hexamethyl-3—((trimethylsilyl)oxy)trisiloxan—-3- yl)propyl)amino)-N,N- 5 dimethyl-6-oxohexan—1-aminium salt (surfactant 2) L CONTR Live Quartz for healthy mops surfactant; | ; 5N DSHCRS Moi Alice 8 Ad 1 Atat Wawa Po HOI B ey Hey Red Any Dam HERRIOT Plus I i Bs B Surfactant + Dissolved 6- (Dimethylamino) Hexanotic Acid 6- (Dimethylamino)hexanoic (20 800) 2.00 g; 12.56 mmol”; 1 equivalent) in toluene (50 milliliters) in a beaker

— 2 6 —

100-milliliter round-bottom boiler supplied with a Dean Stark trap; And then add 3-amino pubyl tris

(trimethylsiloxy)silane (aminopropyltris(trimethylsiloxy)silane—-3) 5.48 milliliters

1 mmol » 1.1 eq.). The reaction vessel is heated; The reaction will return for 24 hours until it does not take place

Separation of more water in the pipe of Dean Stark. The solvent was removed under reduced pressure to obtain

On the surfactant 1 yellow turmeric with a yield of 9694. 11 Analysis

Nuclear magnetic resonance (NMR) spectroscopy (500 MHz).

Hz (gla methyl sulfoxide (axl) 6:0.09 (dimethylsulfoxide (DMSO) 27 h) –

0.31-0.28 (m:2h) – 1.26-1.12 (2¢p) h) – 1.30-1.27 (m; 4h) – 1.38

1 (m; 2 hours) – 1.94 = J t) (7.3 Hz 2 hours); 2.00 dul) 6 hours); 2.06 0 - 2.03 (m; 2 h ); 2.89 (ia) l - ¢12.9 6.8 Hz 2 h).

in its neutral form; Surfactant 1 is slightly soluble in pure water without

Addition of aqueous drops or cal surfactants, but after the addition of a proton under conditions

Slightly acidic it becomes interfacial active (surfactant 2). Acidic conditions can be created

By adding any acidic buffer or acid in the pH range of 4-7. Surfactant 5 can also be prepared in non-aqueous solutions; An example of a spare Gob

The gaseous hydrochloric acid in toluene has a hypotonic effect

surfactant 1.

Example 1b:

Determine the critical micelle concentrations (CMC) of surfactant 0 surfactant 2

Critical micelle concentrations (CMC) of the surfactant were tested

for surfactant 2 using an anti-chloride ion and was determined to be about 2 mM

mall. dad reaches the relatively stable level of minimum surface tension that can be reached (ad).

With this surfactant, about 23 milliN/m. Figure 1: A plot of these results; Shows surface tension versus concentration. Example 2a: Synthesis of 6-((3-(1,1.1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-NINN-tri methyl-6-oxohexane-1-aminoiodide-680-3HA5aa( BD(a5a1107181))-3-a1,1,1,5,5,5-68076)-3))-6 yhpropyl)amino)- N,N,N-trimethyl-6-oxohexan—1-aminium iodide (3-surfactant) © M Sher and Jen Nass Einat B Tl and Rommmm Hi ee Po “ERT ain Shee YOR en surfactant + surfactant 1

0 "salad) surfactant 1 (1.00 g; 2.02 mmol; 1 equiv) was dissolved in acetonitrile (10 mL) in a 100 mL round-bottom flask. Then, sodium carbonate was added. 2a 0.26) Sodium carbonate (Na2CO3) 2.42 mmol 2 eq) and the mixture s.d. was stirred for 10 minutes. Add methyl iodide (0.377 mL. 6.06 mmol; 3 eq.) and the reaction was heated at 40 ° s.l.e. 24 hours Done

5 Filtration of the cooled reaction mixture; and removing the solvent under reduced pressure to obtain the surfactant 3 as a slightly yellow solid in the quantitative yield. 11Nuclear magnetic resonance (NMR) spectroscopy (500 MHz (gla) dimethylsulfoxide (DMSO) 6: 0.09 (sec; 27 h) – 0.38- 2¢p) 0.42 h – 1.26-1.23 2¢p h) – 1.40-1.37 (m; 2h) – 1.55-1.52 (m;

0 2h)-1.69-1.65 (5 2h)-2.08 ot) l-7.4 Hz 2 (in) 2.99 (dela = J 13; 6.9 hr)- 3.04 (s; 9 hours) 3.24 - 3.33 (m; (dela

— 8 2 — The pure product is soluble in water and has surfactant properties. The halogen anions can be obtained directly from the L1-alkylation reaction (Sarge). The desired anti-GAY anions can be obtained by anion exchange. Example 2b: Determination of the physical properties of the aha surfactant 3 The critical micelle concentration was measured micelle concentrations (CMC) of the surfactant 3. From the change of surface tension with concentration in water, the CMC was determined to be about 6 mmol. The value of the relatively stable level of minimum surface tension that can be reached by this surfactant The surfactant has a surface tension of about 20 mN|m, which indicates that the surfactant has distinct interfacial activity These results are plotted as surface tension versus concentration in Fig. 2. The dynamic surface gall of the surfactant 3 was determined Using a bubble pressure tensiometer that measures the change of surface tension of a newly created air-water interface with time Figure 3 plots the results as surface tension vs. time and shows that the surfactant 3 may completely saturate the interface in less than 500 ms; Which makes them exceptionally fast in terms of interfacial absorption. In addition to the ability of the surfactant 3 to reduce the tension between two surfaces and the surfactant »; All formulations contain lid surfactant, which has exceptional wetting properties. For example; Non-hydrophobic substrates such as polyethylene and polypropylene show wetting by shall GIS with a contact angle of 0°. On non-hydrophobic and oleophobic substrates such as Teflon, the contact angle measured was very low; 0.5 1° (Table 2). Table 2

— 9 2 — ‎sald) antihypertensive | dll angle of depressor | Focus angle of surface contact ‎surfactant | Surface tension 3 (degrees) of water (degrees) Polyethylene 10x CMC 91.5 Polyethylene Polypropylene 10x CMC |93.3 Polypropylene Polyethylene Terephthalate 10x CMC |65.3 Polyethylene terephthalate Example 3a: Synthesis of 6-((3-(1,1.1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-NIN-dimethyl -6-oxohexane-1-amine oxide -6 ((3-(1,1,1,5,5,5-hexamethyl-3—((trimethylsilyl)oxy)trisiloxan—3- yl)propyl)amino )-N,N-dimethyl-6-oxohexan—]1-amine oxide 5 (surfactant 4) J and M Rly 77 Daqamis L P HSI HSI ee Will ee TT i.e. ERGOT ae : : 5 (WR surfactant an surfactant; surfactant pa 1.00) 1 surfactant 2.02 m(dss 1 eq) was added to distilled water) 80 milliliters) in a 100-milliliter round flask; followed by the addition of 17650

— 0 3 — hydrogen peroxide (1.15 milliliters 20.2 mmol; 10 eq). The reaction was held back for 12 hours; Hence the concentration was done at reduced pressure. The residue was washed three times with acetone to obtain sald surfactant 4 with a yield of 9. 1-1 Nuclear magnetic resonance (NMR) spectroscopy 5 (500 MHz) gla methyl Sulfoxide (dimethylsulfoxide (DMSO) § 0.09 (dul) 27 h) – 0.44-0.38 <p) 2 h) – 1.25-1.21 (m; 2 h) – 1.42-1.35 (m; 2 h) - 1.55-1.50 (m; 2h) → 1.75-1.71 (m; 2h) → 2.08-2.05 <p) 2h) → 3.00-2.97 (m; 2h) → 3.01 aul) 9 hours ) 3.11 = 3.14 (m » 2 hours). DM: 0 Determine the physical properties of the surfactant Abul 4 The critical micelle concentrations (CMC) of the surfactant 4 were measured from the change in surface tension with concentration in water; The CMC was determined to be about 9 mmol. The value of the relatively stable level of minimum surface tension that can be reached by this surfactant is about 20 mN | M; Which indicates that the surfactant has distinct interfacial activity. These results are plotted as surface tension versus concentration in Fig. 2. The dynamic surface tension of surfactant 4 was determined using a bubble pressure surfactometer. Figure 5 plots the results Jie surface tension vs. time and shows that the surfactant 4 completely saturates an air-water interface 0 created aa in 1 second or less; Which makes it fast in terms of interfacial adsorption. In addition to the ability of the surfactant 4 to reduce both the tension between two surfaces and the surfactant »; All formulations contain only surfactant 4 in concentrations from 1 - 100 x Low Critical Micelle Concentrations (CMC) CRITICAL MICELE CONCENTRATIONS have exceptional wetting properties. for example

— 1 3 — example; A solution of surfactant 4 in water at a concentration of 10x CMC shows a contact angle of 0 Jo da) hydrophobic_substrates Jie polyethylene and polypropylene “10.6° on hydrophobic Jie substrates Teflon 1610107. These contact angles are very low compared to the contact angle of water on the same substrate (Table 3). Table 3 Surfactant | 10x CMC |91.5 Polyethylene 10x CMC [93.3 Polypropylene 10x CMC | 65.3 Polyethylene terephthalate Example 4A: Glas 4 -((6) -((3-(1,1.1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)proyl)amino)-6-oxohexyl)dimethylammonio)butane - 1 Sulfonate 4-((6-(((3-(1,1,1,5,5,5-hexamethyl-3)—( (trimethylsilyl) oxy)trisiloxan—3-

yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate (surfactant 5) LA So pose SOU fr sat ta surfactant Sg > surfactant gt Surfactant 1 Surfactant 1 (1.00 g; 2.02 mmol; 1 equiv) was added to ethyl acetate (EtOAc) 5 (30 mL) in a 100 mL round flask; followed by the addition of 1,2-butane sultan (0.27 milliliters » 2.2 mmol); 1.1 eq). The reaction was held back for 12 hours; The solvent was then removed and the resulting white waxy solid was washed with acetone to yield surfactant 5 with a yield of 90650. Nuclear magnetic resonance (NMR) spectroscopy (500 MHz; dimethyl sulfoxide aut 0.10)11 5 (dimethylsulfoxide (DMSO) 0 27 hr) – 0.46-0.38 (m; 2 hr) → .1.27-1.23 (m 2 hr) – 1.37- 1.68 (m 10 hr) 1.78-1.73 (m 2 hr) ) »» 2.48-2.45 (m 2 hours) → 3.01-2.97 (m 8 hours) → 3.21-3.18 (m 2 hours) → 3.27-3.23 (m » 2 hours). Example rod 5 Determination of Physical Properties of Surfactant 5 Critical micelle concentrations (CMC) of Surfactant 5 were measured from the change in surface tension with concentration in water; The CMC was determined to be about 0.39 mmol. The value of the relatively stable minimum surface tension that can be reached by this surfactant is about 21 m pf iss 20 which indicates that the surfactant has distinct interfacial activity. These results are plotted as surface tension versus concentration in Figure 6.

— 3 3 — The dynamic surface tension of Surfactant 5 was determined using a bubble pressure tonometer. Figure 7 plots the results as surface tension versus time and shows that surfactant 5 completely saturates a newly created air-water interface in 1 second or JB making it fast in terms of interfacial adsorption.

hal 5 surfactant solution 5 in water at reduced critical micelle concentrations (CMC) CRITICAL MICELLE CONCENTRATIONS 10 exhibits a contact angle of 0° on hydrophobic substrates such as polyethylene and polypropylene These contact angles are very low compared to the contact angle of water on the same substrate (Table 4).

0 table 4 anti-stress substance | contact angle of a depressor | Concentration Surface Contact Angle 1 surfactant Surface Tension 5 Water (degrees) (degrees) Polyethylene x CMC 10 91.5 Polyethylene Polypropylene x CMC 10 93.3 Polypropylene Polyethylene Terephthalate x CMC 10 65.3 Polyethylene terephthalate

— 4 3 — Polyethylene x CMC 10 93.6 HD-polyethylene Example 5: The shampoo formula in this example; Formula is provided for use as a shampoo. This formula is beneficial in giving the hair a soft and silky feel. The ingredients of the formulation are listed below in Table 4. Additionally; Formula may include oils and other natural ingredients; In addition to vitamins to attract the consumer; in quantity less than 961 wt. Table 4 Surfactant Surfactant 10-1 Ssurfactant Blowing Agent 25-10 Ammonium lauryl sulfate ISS Amido. Proyl Betaine | Combined stress reliever | 5-0.1 Cocamidopropyl betaine surfactant. Diethanolamine | Foam Booster 4-1 Cocamide diethanolamine

— 5 3 — Xanthan gum or | Thickener / Rheology Modifier 1 5 cub Sf Copolymer acrylate copolymer Citric acid pH Stabilizer 0.3-0.1 m: ’ | ’ ] ’ | ’ ] ’ ’ JE 6: The conditioner formula in this example; Formula is provided for use as a hair conditioner. This formulation can be used to replace or reduce Polyquaternium-10 oils 700816001000-10A00 _ Polyquaternium-7 and hair. The formula is shown below in Table 5. Table 5 Surfactant | Surfactant 10-1 3surfactant Surfactant | Surfactant 10-1 surfactant 5 Sodium Cumin Sulfonate | Hydrotrope 3-1 cumene sulfonate

— 6 3 — ammonium lauryl sulfate | Surfactant |6-0.1 Ammonium lauryl sulfate upd apse lugs -3 | Surfactant 6-0.1 Ammonium laureth-3 sulfate Cocamide. Diethanolamine | Foaming Agent 2-5 Cocamide Diethanolamine 56-5 Oleate Propylene Glycol | Emulsion 1-0.01 propylene glycol oleate m : ’ | ’] | ’ ’ | ° ] : | ' JE 7: A car wash detergent formula for removing tough surface stains in this example; A formulation is provided for using car wash detergents to remove tough stains from the surface. The formula is shown below in Table 6. Table 6 Surfactant | stress reliever | 0.1-10 Ssurfactant Dodecyl benzene sulfonic acid Foaming agent / disinfection 1 5- 14 benzene sulfonic acid or

— 7 3 — Ammonium lauryl sulfate monoethanolamine | Monoethanolamine or Diethanol | pH . >0.5 diethanolamine or triethanolamine Cocamide | Foam stabilizer 2-1 diethanolamine propylene glycol dissolving agent 1.6-0.05 : ’ | ’ ] ee ee ° | ] ’ | ’ ’ JE 8: Formula for the spot-free rinse or drying solution in this example; Spot-free rinse or dry solution formula provided. The solution can be applied to the windows or the body of the car after the main wash is completed. The formula is shown below in Table 7. Table 7 Article | Surfactants | 2-1 Surfactant Ssurfactant

— 8 3 — ’ ] ’ ’ | Example 9: Heavy duty carpet cleaner formulation in this example; Heavy duty carpet cleaner formula provided. The cleanser is a high foaming deep cleanser. The formula is shown below in Table 8. Table 8 Article | anti-stress | surface | 1 15-1 4surfactant, surfactant, Dodecyl benzene sulfonic acid or foaming/disinfecting agent | 10-0.001 Ammonium lauryl sulfate Sodium cumene sulfate | Hydrotrope 3-1 Cumene Sulfonate Monoethanolamine | Monoethanolamine or Diethanol | hydrogen 1-1 amine diethanolamine or triethanolamine ’ ’ | ’] Jia 10:

— 9 3 — Heavy-duty surface cleaner formulation in this example; A heavy-duty surface cleaner formulation is provided. This cleaner can be used in manual or automatic surface cleaning machines. The formula is shown below in Table 9. Table 9 Surfactant | 25-1 4surfactant Dodecyl benzene sulfonic acid or foaming/disinfecting agent | 10-0.001 Ammonium lauryl sulfate Sodium cumene sulfonate 5001000 | Hydrotrope >0.5 cumene sulfonate (lug ll) glycol propylene glycol dissolving agent 5-0.01 water 59.5- 29.9 Example 11: Concentrated Graffiti Remover Formulation In this example, a formulation of a concentrated graffiti remover cleaner is given. The detergent can be used in a high-pressure hose.The formula is shown below in Table 10. Table 10

— 0 4 — Surfactant | surfactant 15-1 4surfactant surfactant 7 surfactant | Co-Wetting Agent | 10-0.001 surfactant 5 Sodium cumene sulfonate Sodium hydrotrope 3-1 cumene sulfonate propylene glycol | propylene | Dissolving agent 3-1 glycol ‘ ° ] ’ ’ | Example 12: Formulation for a wetting agent in aerosol sprays in this example; A formulation for a wetting agent is provided in aerosol sprays. Mist sprayers may be used to apply pesticides or other crop protection agents. The presented formulation aims to reduce the amount of surfactant chemicals in pesticides and crop protection (usually between 965-2) by providing better performance through excellent wetting and low percentage of critical micelle concentrations «(CMC) CRITICAL MICELLE CONCENTRATIONS ll provide a greener option. The formula is shown below in Table 11. Table 11

— 1 4 — Article | Surfactants | Wetting agent © 2-1 surfactant 2 4” or 5 co-pesticide and/or other agent(s) 1-10 for crop protection] ‘’ Example 13: Spray paint additive formulation in this example; A sald formula is provided as an additive to paint or paint with an aerosol spray consisting mainly of sll. The composition aims to provide a good dynamic wetting of the aerosol droplets on the surfaces upon application; Thus preventing paint craters and other similar problems. The formula is shown below in Table 12. Table 12 Surfactant | Wetting agent / flow leveling agent. ’ 5-1 “4surfactant or 5 / Slip Control Agent” - B 7 a | 5 Efka SI12022 or 2723 Sl 2-1 Antifoam Agent

— 2 4 — Sides A side of 1 is a compound with Gall b QEHTH, pm m 0 obituary TyTN log 0 formula where l and R? can be the same or different” Pliny on one group At least selected from the group consisting of an alkyl “C1-C6 alkyl Optionally, the alkyl 01-6 may include one or more oxygen, nitrogen, or sulfur atoms or groups 501007 which contain at least one of these atoms; The alkyl chain may optionally be substituted with one or more substituent groups selected from the group consisting of hydroxyl amino camido camido sulfonyl sulfonate 0 carbonyl creoxyl carboxyl and creoxylate 081507/1816?; N is an integer from 1 to ¢12 Optionally Load substitutes the final nitrogen (RY), where RY is La) of the group consisting of hydrogen, oxygen, and hydroxyl talkyl C1-C6 (<li, and an arbitrary counterion may be associated with the compound and if present; the counterion 07 can be selected from the group consisting of chloride, bromide and iodide Side 2 is a compound According to side 1 is represented by the form tla

— 3 4 — oe ISHED dj a 1 Co l (HChSI0. yd TN 7 sbd (FSCS) a 0 form la where RY and R could be are the same or different” and include at least one group selected from group ll consisting of an alkyl “C1-C6 alkyl Optionally an alkyl 01-6 can include one or more oxygen atoms or groups or nitrogen 5 or sulfur containing at least one of these atoms; the alkyl chain may be substituted

an alkyl optionally with one or more substituent groups selected from the group consisting of hydroxyl, amino, camino, camido, sulfonyl, sulfonate, creonyl Al68+001, carboxyl, and creoxylate. scarboxylate represents 177 whole numbers from 1 to 6;

10 The final nitrogen is optionally substituted additionally by RY ; Where is selected from the group consisting of hydrogen, oxygen, and an alkyl C1-C6 where the alkyl chain is optionally replaced by one or more substitution groups selected from the group All consisting of ccarboxyl carboxylate and ¢sulfonate and

5 An arbitrary counterion may bind to the compound and if present; The antiion 07 can be chosen from the group consisting of chloride, bromide, and iodide. Side 3 is a compound according to either side 1 or 2 represented by formula 0a:

05 b yemi l l y {MCS Se HR N ' b oy merh The Naknad 0 © formula where RY and R? can be the same or different' and include contains at least one group selected from group ll consisting of an alkyl “C1-C6 alkyl Optionally the alkyl 01-6 may include one or more oxygen or nitrogen atoms or groups 5 or sulfur containing at least one of these atoms; The alkyl chain may optionally be substituted with one or more substitution groups selected from the group consisting of hydroxyl amino camino camido sulfonyl sulfonate creonyl Al68+001 creoxyl carboxyl and scarboxylate m is 5;

10 The final nitrogen is optionally substituted further with RY whereby the group consisting of hydrogen, oxygen, 007/9617 and an alkyl -61 (C6) is chosen where the alkyl chain is optionally substituted with one or more substituent groups selected from group All consisting of a carboxyl carboxylate, a sulfonate, and

An arbitrary counterion may bind to the compound and if present; The antiion 07 can be chosen from the group consisting of chloride, bromide and iodide Side 4 is the compound according to any of the sides 3-1 where RY and »| A methyl of side 5 is the compound according to side 1; Where 0 equals 5.

0 Side 6 is the composite according to any of Sides 1-5; RY Gus is hydrogen

Side 7 is the compound according to any of sides 1-6) where the counterion is chosen from the group consisting of chloride, bromide and iodide Side 8 is the compound according to side 7 Gua be The counterion is chloride 5. Side 9 is the compound according to either side 1-5 (where R306 is methyl

Side 10 is the compound according to Side 9; The anti-ion cOUNterion is selected from the group consisting of chloride, bromide and iodide. Side 11 is the compound according to side 10; Where the counterion is iodide

Side 0 12 is the compound according to any of sides 5-1 where ple RY is about an oxygen atom . Side 13 is the compound according to any of sides 5-1 where RY is a C6 -01 alkyl Jaws alkyl peripheral sulfonate. Side 14 is the compound according to either side 1-3 where the compound is 6-(dimethyl

(sd 5 -l- ( -3-(1,1.1, 5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-(dbpropyl)hexane ad - 1,1,1,5,5,5)-3)-L1-(200100un010761)-6 hexamethyl-3—((trimethylsilyl)oxy)trisiloxan—-3-yl)propyl)hexanamide « . has the following formula :

OSi(CH (HsC)sSI0L HCH) \ (H3C)3Si0" 7 ~~ hha NT 0 0 Side 15 is the compound according to either side 8-6, where the compound is 6-J)methyl

Amino)-L-( -3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)tri)

siloxane-3-yl) (dug p hexaminium chloride 6-(dimethylamino)-N—(3- (1,1,1,5,5,5-hexamethyl-3—((trimethylsilyl)oxy) trisiloxan—-3- yl)propyl)hexaminium chloride ; has the following formula: © : y @ Cl and (HyC)pSI0g b yl s s s "> ~~ tqoroui) 0. Side 15 is the compound According to either aspect 11-9, wherein the compound is 36-((3-(1,1.1,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-propyl)amino) NNN - - Tri Jie -6- oxohexane-1-aminoiodide -1,1,1,5,5,5)-3))-6 3 hexamethyl-3—((trimethylsilyl)oxy)trisiloxan— 3-yl)propyl)amino)-N,N,N- trimethyl-6-oxohexan—1-aminium iodide ¢ has the following formula: © : o nat enum (H3C)3Si0” ~~ hd N 4 | 0 side 17 is the compound according to side 12 (where the compound is 6-((3-)1,1.1 5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl) propyl)amino) = no-trimethyl-6-oxohexane-1-amine oxide 6-((3-(1,1,5,5,5-hexamethyl-3— ((trimethylsilyl)oxy)trisiloxan— 3-yl)propyl)amino)-N,N-dimethyl-6- oxohexan—1-amine oxide 5 « has the following formula: 0 yo nc ~~ a n, n-dimethyl-6- oxohexan—1-amine oxide 5 « has the following formula: 0 is Compound according to side 13 (where the compound is 4-((6-((3- (1,1.1, 5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino) - 6-oxohexyl)dimethylammonio)butane-1-sulfonate-1,,1,1,5,5,5)-3)-6)-4

hexamethyl-3—((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)-6- oxohexyl)dimethylammonio)butane-1-sulfonate « has the following formula: i(CH (Hi0)810.2 ° for 1 ° © (H3C)3Si0” ~ TON dhe 3 0 ,1.1.1) -3(((-6()- 5 Side 19 is the compound according to side 13, where the compound is hexamethyl- 3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-5,5.5-5-oxohexyl)dimethylammonio)pentane-1-sulfonate has the following formula: - 6 -

OSi(CH (HyC)sSI0.L (CHa), 0 © 5

H 5 Cc ) 5 50 AA No Y N dh SO 3 0

Claims (1)

— 8 4 — Claims 1- A compound with the formula: DAWAN 5 0 AA AA epee NR hi : N b {H;CRSI0 0 Sua where RY and can be R? are the same or different” and contain at least one group selected from the group All consisting of an alkyl “C1-C6 alkyl Optionally the alkyl 5 01-06 can have one or more atoms or oxygen, nitrogen, or sulfur groups 501007 containing at least one of these atoms; The (Glas) alkyl chain may be substituted with one or more substituent groups selected from the group All consisting of gud hydroxyl 800100; amido sud sulfonyl sulfonate csulfonate carbonyl creoxyl carboxyl and scarboxylate carboxylate N 10 an integer from 1 to 12” is also optionally substituted for the final nitrogen RY, where RY La) is formed from the group consisting of hydrogen, oxygen, hydroxyl, and a C1-C6 alkyl; An optional counterion may bind to the compound; and if cng the counterion 5 can be chosen from group All consisting of chloride, bromide and iodide 2 - compound according to claim 1; Represented by the form tla QBHCH Fly and min HO RT to count only N ’ 7 2 mah {FCS ow” 0 form la where RY and #8 can be the same or different” and contain at least one group Selected from the group consisting of an alkyl «C1-C6 alkyl optionally may include an alkyl 01-6 contains one or more oxygen or nitrogen atoms or groups or Sulfur 501503 containing at least one of these atoms; The alkyl chain 5 may optionally be substituted by one or more substituent groups selected from the group comprising of gud hydroxyl 800 100; amido sud sulfonyl sulfonate scarboxylate and creoxylate carboxyl carbonyl creonyl csulfonate Jia 17 is an integer from 1 to 6; The final nitrogen is optionally additionally substituted with RY where ROL is made from 0 group consisting of hydrogen, oxygen, and a 61-06 alkyl wherein the alkyl chain is optionally substituted by one or more substitution groups selected from the carboxyl group consisting of a carboxyl “carboxylate and ¢sulfonate” and the compound may be linked to an anti-ion “(glial counterion) and if it exists, the anti-ion can be chosen counterion 5 of the group consisting of chloride, bromide and iodide 3 - the compound of claim 1; represented by the form 0a: For ORSON hf RR mah {FU a 0 formula a 0 where RY and “#8 can be the same or different” and contain at least one group selected from the group consisting of an alkyl “C1-C6 optionally the alkyl 01-6 can include One or more oxygen, nitrogen, or sulfur atoms or groups 501503 that includes at least one of these; the alkyl chain may be substituted alkyl chain optionally with one or AST substituent groups selected from the group consisting of hydroxyl gud hydroxyl 800100; amido sud sulfonyl sulfonate csulfonate carbonyl carboxyl carboxylate and scarboxylate m are 3) the final nitrogen is optionally substituted further with RY whereby 3c is chosen from the set consisting of hydrogen, oxygen, and an alkyl 01-6, wherein the alkyl chain is optionally substituted by one or more substituent groups selected from the carboxyl group consisting of “carboxyl” carboxylate and ¢sulfonate and 0 may bind to the compound an optional counterion ion; and if cag the anti-ion 07 can be chosen from the group consisting of chloride, bromide and iodide 4- the compound according to of claim 1, where a and 4 are methyl 5 - compound of claim 1; N Cus equals 5. 6 - compound of claim 5 where RY is hydrogen 0 7- The compound according to claim 6, where the counterion ion is chosen from the group consisting of chloride, bromide, and iodide 8- The compound according to claim 7 Cus, the counterion ion is chloride .chloride 5 9- The compound according to claim 5 where R? is methyl — 5 1 — 0- the compound according to claim 9) where the antiion, cOUNterion, is chosen from the group consisting of chloride, bromide, and iodide 1- the compound according to claim 10, where the antiion is counterion is iodide 5 2- the compound according to claim 5 where RY is an oxygen atom .oxygen atom 3- the compound according to claim 5 where 3 is a C1-C6 alkyl substituted with a sulfonate .sulfonate 0 4- Compound of claim 5; where the compound is 6-(dimethylamino) “N= )= 3-)1.1.1, 5,5.5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl ) hexaneamide 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)hexanamide 5 ¢ has the following formula: (H3C)3Si0" | 0 5- the compound of claim 8, where the compound is 6- (dimethyl N= (sid )= 3- )1.1.1, 5.5.5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)0-propyl)hexaminium chloride 6-(dimethylamino)-N—-(3-(1, 1,1,5,5,5-hexamethyl- 3—(((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexaminium chloride « has the following formula: © (HiC)SIOg 2 0 ® Cl (H5C)3Si0” bide N b 8 — 2 5 — 6- Compound of claim 11; where the compound is 36-((3- )1,1.1 5,5,5- hexamiphyl -3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amine) - NNN - trimethyl -6-oxohexane-1-aminoiodide 6-((3-(1,1,1,5,5,5-hexamethyl-3—3 ((trimethylsilyl)oxy)trisiloxan—3-yl)propyl) amino)-N,N,N-trimethyl-6—- 5 oxohexan—1-aminium iodide; It has the following formula: © : (HiC)SI0. 3 10% 0 ® 1 hdd NC ~~ awn'rhum) 7- The compound according to claim 12 (where the compound is 6-((3- (1,1.1, 5,5.5- 0-hmsa-methyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl) amino) = NN -trimethyl-6-oxohexane-1-amine oxide 6-((3-(1,1,1,5,5,5-hexamethyl-3—((trimethylsilyl)oxy) )trisiloxan—3-yl)propyl)amino)-N,N-dimethyl-6- oxohexan—1-amine oxide « has the following formula: (HAC)SIO J OR 0 (H3C)sSi0” ~~ hdd NC ©0- | 0 8. The compound of claim 13; where Spall is 4 -((6-((3- (1,1.1, 5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)- 6-oxohexyl)_dimethylammonio)butane-1-sulfonate-1,1,1,5,5,5)-3))-6))-4 hexamethyl-3—((trimethylsilyl)oxy)trisiloxan—3 -yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane—1-sulfonate 20 ; It has the following formula: GRO RAY ® 6 0 ASIN ASN (H3C)3SiO TON 0 — 3 5 — 9- The compound according to claim 13 where the compound is 5-((6-((3-)1,1.1 5,5,5- hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3 - yl)propyl)amino)-6-oxohexyl)AE methylammonio)gly-1 sulfonate-1,1,1,5,5,5)-3)-6)-5 hexamethyl-3 —((trimethylsilyl)oxy)trisiloxan—3-yl)propyl)amino)-6- oxohexyl)dimethylammonio)pentane—1-sulfonate 5 « has the following formula: (HAC)SIO LOR 0 ® © Lv ANN (H5C)3Si0"" ~~ YO N SO; \ 7 0 _— 4 5 _— Gq . Gq Wa iia. 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Fig. 1 : 3 - © — 5 9 — CIO sed ' and | Re : 3 ee d ' % ; : ا ْ ْ % Lg | M: A | 5 À BB | > : &, ¥ ~ º > % : Then º Bi : Ye º Be . 8 a #8 ; oaeta grogg tae WN hE Tenn Sones ex gE lil ya © wd nd b “ 1 “i yf 3 a 1 A eee ْ 3 what he Se Ca \ ِ e 3 ly a ly oR l and " º : 3 De wf % 1 1 \ z : 1 : 4 A 3 : 8 : 1 !a = Yao 3 : 3 X  Pod Tad %  | Yo a : x x8 3 % \ yp 3 : i Ya sell Yaa LERNER jaw dose  1 on the vessel I Btah of BE 5 § The Saudi Authority for Intellectual Property Sweden Authority for Intellectual Property pW RE .¥ + \ A 0 § Um 5 + < Ne ge “Benaj > Aye Ki Jada Li Days TEE Bbha Nase eg + Ed - 2 - 3 .++ .* provided that the annual financial fee is paid for the patent and that it is not null and void due to its violation of any of the provisions of the patent system, layout designs of integrated circuits, plant varieties and industrial designs or its implementing regulations. »> Issued by + BB 0.B Saudi Authority for Intellectual Property > > > “+ PO Box 1011 .| for ria 1*1 uo ; Kingdom | Arabic | For Saudi Arabia, SAIP@SAIP.GOV.SA